US4301144A - Blood substitute containing modified hemoglobin - Google Patents
Blood substitute containing modified hemoglobinDownload PDFInfo
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- US4301144A US4301144AUS06/167,360US16736080AUS4301144AUS 4301144 AUS4301144 AUS 4301144AUS 16736080 AUS16736080 AUS 16736080AUS 4301144 AUS4301144 AUS 4301144A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/795—Porphyrin- or corrin-ring-containing peptides
- C07K14/805—Haemoglobins; Myoglobins
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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- This inventionrelates to a novel blood substitute containing a modified hemoglobin as an oxygen-carrying material.
- modified hemoglobinwhen hemoglobin is combined with a polyalkylene glycol or its derivative (hereinafter referred to as "modified hemoglobin"), the oxygen-carrying ability of the modified hemoglobin is nearly equal to that of the original hemoglobin, and the residence time in the circulation is satisfactorily long.
- the polyalkylene glycol and its derivative applicable to the inventioninclude polyethylene glycol, polypropylene glycol, a copolymer of ethylene glycol and propylene glycol, an ether of one of the above-mentioned polyalkylene glycols and an alcohol having a carbon number of 1 to 16, such as monomethyl ether, monocetyl ether and monooleyl ether, an ester of one of the above polyalkylene glycols and a carboxylic acid having a carbon number of 2 to 18, such as monobutyl ester and monostearyl ester, and a dehydrated product of one of the above polyalkylene glycols and an amine having a carbon number of 1 to 18, such as propylamine and stearylamine.
- polymer employed in the inventionMolecular weight of the polymer employed in the invention is usually 300 ⁇ 20,000, preferably 750 ⁇ 5,000 in terms of elongation of residence time in circulation.
- the hemoglobin applicable to the inventionincludes those of human, cow, swine, sheep, horse, dog, monkey, rabbit, and hen.
- the hemoglobin and the polymer employed in the inventionmay be coupled by any means, and for example, they are directly combined using a condensing agent such as cyanogen bromide, or they are combined using a cross-linking reagent such as cyanuric chloride, 2,2'-dichlorobenzidine, p.p'-difluoro-m,m'-dinitrodiphenylsulfone and 2,4-dichloronitrobenzene. 4 to 120 molecules of the polymer employed in the invention are combined to one hemoglobin molecule.
- a condensing agentsuch as cyanogen bromide
- a cross-linking reagentsuch as cyanuric chloride, 2,2'-dichlorobenzidine, p.p'-difluoro-m,m'-dinitrodiphenylsulfone and 2,4-dichloronitrobenzene.
- the modified hemoglobinmay be prepared according to the following methods:
- Polyethylene glycolis reacted with 2 to 5 times moles, preferably 3 times moles of cyanogen bromide at pH 9-10. Residual cyanogen bromide is removed from the reaction mixture by gel filtration, dialysis, etc., and then the product is reacted with 1/10-1/500 time mole, preferably 1/50-1/100 time mole of hemoglobin at pH 7-9, preferably 7.5-8 in an aqueous solution.
- the modified hemoglobinis easily soluble in water, and color of the solution is red.
- the modified hemoglobinis a nontoxic material, and the reason is that the modified hemoglobin is a combined matter of hemoglobin separated from a living body and the polymers employed in the invention which are highly nontoxic. Since oxygen affinity of the modified hemoglobin is nearly equal to or slightly stronger than that of natural hemoglobin, the modified hemoglobin is preferable for carrying oxygen to tissues. Furthermore, the residence time of the modified hemoglobin in the circulation is about 2-4 times longer than that of stroma free hemoglobin itself. As described above, the modified hemoglobin is preferable material for a blood substitute. In particular, it is known that a protein modified by polyethylene glycol loses the antigenicity of the protein (A. Abuchowski et al., J. Biol. Chem., vol.
- the number of polyalkylene glycol attached to hemoglobin described in the Exampleswas determined as follows: The concentration (Co) of a modified Hemoglobin solution was determined by the cyanomethemoglobin method, and the weights of the modified hemoglobin (Mo) was measured after freeze-drying of v 0 ml of the solution. Thus, the number of polyalkylene glycol (N) is: ##EQU1## where M 1 and M 2 are the molecular weights of polyalkylene glycol and hemoglobin, respectively.
- the concentratewas diluted with 300 ml of phosphate buffer solution of pH 7.5, and then concentrated to 20 ml by the ultrafiltration again. 20 ml of 10% aqueous solution of human hemoglobin were added to the concentrate while the concentrated solution was stirred and chilled in an ice bath. The reaction mixture was then allowed to stand overnight at 4° C. Subsequently, the reaction mixture was passed through a column where CM-Sephadex gel was packed and pre-equilibrated to pH 6.0. The column was eluted with 0.05 M phosphate buffer solution of pH 6.8 and the fractions of the modified hemoglobin were collected. The fractions were desalted and concentrated by ultrafiltration using A-15T membrane of which cut-off molecular weight is 15000 dalton.
- the concentratewas filtered through a 0.45 ⁇ membrance, and the filtrate contained 3.5 g of a combined material of hemoglobin and polyethylene glycol monomethyl ether as a dried matter. About 10 molecules of polyethylene glycol monomethyl ether were combined with one hemoglobin molecule.
- the reaction mixturewas concentrated by ultrafiltration using XM-100 membrane (made by Amicon Co.) and the modified hemoglobin in the reaction mixture was adsorbed on a column of CM-Sephadex gel which was pre-equilibrated with 0.05 M phosphate buffer solution of pH 6.0. The first fraction of elution using pH 6.3 phosphate buffer solution discarded, and the next fraction using pH 6.8 phosphate buffer solution was collected. The fraction was concentrated by using the XM-100 membrane, and 3 g of the modified hemoglobin were obtained as a dried matter. About 4 molecules of polyethylene glycol were combined with one hemoglobin molecule.
- Example 2Using 12.5 g (0.005 mole) of polyethylene glycol monostearyl ester of which the mean molecular weight is 2,500, 400 ml of benzene, 5 g of sodium carbonate and 2.75 g (0.015 mole) of cyanuric chloride, the same treatment as Example 2 was carried out, and accordingly 13.5 g of activated polyethylene glycol were obtained. 10.5 Grams (0.004 mole) of the above activated polyethylene glycol were treated with 25 ml (0.04 mmol.) of 10% hemoglobin solution and 900 ml of borate buffer solution of pH 9.2 in the same manner as Example 2, and 8 g of the modified hemoglobin were obtained. About 52 molecules of polyethylene glycol monostearyl ester were combined with one hemoglobin molecule.
- Example 2Using 5 g (0.005 mole) of polyethylene glycol monooleyl ether of which the mean molecular weight is 1,000, 400 ml of benzene, 5 g of sodium carbonate and 2.75 g (0.015 mole) of cyanuric chloride, the same treatment as Example 2 was carried out, and accordingly 6 g of activated polyethylene glycol were obtained. 5.3 Grams (0.002 mole) of the above activated polyethylene glycol were treated with 1.3 g (0.02 mmol.) of bovine hemoglobin (made by Sigma Co.) and 450 ml borate buffer solution of pH 9.2 in the same manner as Example 2, and 4.2 g of the modified hemoglobin were obtained. About 85 molecules of polyethylene glycol monooleyl ether were combined with one hemoglobin molecule.
- bovine hemoglobinmade by Sigma Co.
- the residence time in a blood vessel and oxygem affinity of the modified hemoglobinswere measured.
- Two rats having an average weight of 350 gwere employed as a sample.
- the ratswere injected with 5 ml of 4-6% modified hemoglobin per kg of body weight of rat through a femoral vein, and each 0.5 ml of blood was withdrawn at 5, 10, 15, 30, 60, 90 and 120 minutes after the injection.
- Each blood samplewas centrifuged, and the concentration of the modified hemoglobin in the plasma was determined by the cyanomethemoglobin spectral method.
- the datawere plotted on a graph, and the half-life residence time of the injected modified hemoglobin in the plasma was determined from the graph.
- the oxygen partial pressure at which the hemoglobin is half saturated with oxygenwas determined by oxygen dissociation curve which was measured by using the apparatus reported by Imai et al (K. Imai, H. Morimoto, M. Kotani, H. Watari, H. Waka and M. Kuroda, Biochem. Biophys. Acta., Volume 200, 189-196 (1970)). The date are shown in Table 2.
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Abstract
Description
1. Field of the Invention
This invention relates to a novel blood substitute containing a modified hemoglobin as an oxygen-carrying material.
2. Brief Description of the Prior Art
It is known to use a blood substitute containing hemoglobin free from stromal components as an oxygen-carrying material (S. F. Rabiner et al. J. Ex. Med., vol. 126, p 1142 (1967)). On the other hand, it is also known that when the hemoglobin is infused into the circulation, it is rapidly excreted through the kidney and metabolized by other metabolic routes. In order to solve this problem, various proposals have been made, for example, a hemoglobin crosslinked with glutaraldehyde (Japan KOKAI No. 76-63920), a hemoglobin coupled with dextran (Japan KOKAI No. 77-51016), and a hemoglobin combined with hydroxyethyl starch (German patent Offenlegungsschrift No. 2616086). However, in the first case, oxygen is difficult to transfer at tissue, because oxygen affinity of the hemoglobin is too tight. In case of the latter two proposals, high concentration of the hemoglobin often leads to unfavorable results because of its high viscosity.
It has now been found that when hemoglobin is combined with a polyalkylene glycol or its derivative (hereinafter referred to as "modified hemoglobin"), the oxygen-carrying ability of the modified hemoglobin is nearly equal to that of the original hemoglobin, and the residence time in the circulation is satisfactorily long.
The polyalkylene glycol and its derivative applicable to the invention include polyethylene glycol, polypropylene glycol, a copolymer of ethylene glycol and propylene glycol, an ether of one of the above-mentioned polyalkylene glycols and an alcohol having a carbon number of 1 to 16, such as monomethyl ether, monocetyl ether and monooleyl ether, an ester of one of the above polyalkylene glycols and a carboxylic acid having a carbon number of 2 to 18, such as monobutyl ester and monostearyl ester, and a dehydrated product of one of the above polyalkylene glycols and an amine having a carbon number of 1 to 18, such as propylamine and stearylamine. The above polyalkylene glycols and their derivatives are hereinafter referred to as "polymer employed in the invention". Molecular weight of the polymer employed in the invention is usually 300˜20,000, preferably 750˜5,000 in terms of elongation of residence time in circulation.
The hemoglobin applicable to the invention includes those of human, cow, swine, sheep, horse, dog, monkey, rabbit, and hen.
The hemoglobin and the polymer employed in the invention may be coupled by any means, and for example, they are directly combined using a condensing agent such as cyanogen bromide, or they are combined using a cross-linking reagent such as cyanuric chloride, 2,2'-dichlorobenzidine, p.p'-difluoro-m,m'-dinitrodiphenylsulfone and 2,4-dichloronitrobenzene. 4 to 120 molecules of the polymer employed in the invention are combined to one hemoglobin molecule.
The modified hemoglobin may be prepared according to the following methods:
(1) Polyethylene glycol is reacted with 2 to 5 times moles, preferably 3 times moles of cyanogen bromide at pH 9-10. Residual cyanogen bromide is removed from the reaction mixture by gel filtration, dialysis, etc., and then the product is reacted with 1/10-1/500 time mole, preferably 1/50-1/100 time mole of hemoglobin at pH 7-9, preferably 7.5-8 in an aqueous solution.
(2) Polyethylene glycol is added to benzene containing excess amount of sodium carbonate, and reacted with 2-5 times moles, preferably 3-4 times mole of cyanuric chloride. The reaction product of polyethylene glycol-4,6-dichloro-S-triazine is then separated, and reacted with 1-1/500 time mole, preferably 1/10-1/100 time mole of hemoglobin in a buffer solution of pH 8-9.5.
The above methods are also applicable to other polymers employed in the invention.
The modified hemoglobin is easily soluble in water, and color of the solution is red. A visible spectrum of the modified hemoglobin consisting of human hemoglobin and polyethylene glycol of which molecular weight is about 4000, is shown in FIG. 1. A13 C nuclear magnetic resonance spectrum of the modified hemoglobin consisting of human hemoglobin and methoxy polyethylene glycol of which molecular weight is about 750, is shown in FIG. 2.
The modified hemoglobin is a nontoxic material, and the reason is that the modified hemoglobin is a combined matter of hemoglobin separated from a living body and the polymers employed in the invention which are highly nontoxic. Since oxygen affinity of the modified hemoglobin is nearly equal to or slightly stronger than that of natural hemoglobin, the modified hemoglobin is preferable for carrying oxygen to tissues. Furthermore, the residence time of the modified hemoglobin in the circulation is about 2-4 times longer than that of stroma free hemoglobin itself. As described above, the modified hemoglobin is preferable material for a blood substitute. In particular, it is known that a protein modified by polyethylene glycol loses the antigenicity of the protein (A. Abuchowski et al., J. Biol. Chem., vol. 252, p 3582 (1977)), and accordingly, there is no fear for the modified hemoglobin to act as antigen in the body. The number of polyalkylene glycol attached to hemoglobin described in the Examples was determined as follows: The concentration (Co) of a modified Hemoglobin solution was determined by the cyanomethemoglobin method, and the weights of the modified hemoglobin (Mo) was measured after freeze-drying of v0 ml of the solution. Thus, the number of polyalkylene glycol (N) is: ##EQU1## where M1 and M2 are the molecular weights of polyalkylene glycol and hemoglobin, respectively.
2.5 Grams (0.003 mole) of polyethylene glycol monomethyl ether of which the mean molecular weight is 750 were dissolved in 40 ml water, and 1 g (0.0095 mole) of cyanogen bromide which was previously dissolved in 5 ml dioxane was added dropwise to the aqueous solution while the solution was chilled in an ice bath. Then, the mixture was stirred for one hour, while the mixture was maintained in the range of pH 9 to 10 using 2 N NaOH. The mixture was adjusted to pH 7.5 using 1 N HCl and concentrated to 20 ml by ultrafiltration using G-05T membrane (made by Bioengineering Co., Ltd.) of which cut-off molecular weight is 500 dalton. The concentrate was diluted with 300 ml of phosphate buffer solution of pH 7.5, and then concentrated to 20 ml by the ultrafiltration again. 20 ml of 10% aqueous solution of human hemoglobin were added to the concentrate while the concentrated solution was stirred and chilled in an ice bath. The reaction mixture was then allowed to stand overnight at 4° C. Subsequently, the reaction mixture was passed through a column where CM-Sephadex gel was packed and pre-equilibrated to pH 6.0. The column was eluted with 0.05 M phosphate buffer solution of pH 6.8 and the fractions of the modified hemoglobin were collected. The fractions were desalted and concentrated by ultrafiltration using A-15T membrane of which cut-off molecular weight is 15000 dalton. The concentrate was filtered through a 0.45μ membrance, and the filtrate contained 3.5 g of a combined material of hemoglobin and polyethylene glycol monomethyl ether as a dried matter. About 10 molecules of polyethylene glycol monomethyl ether were combined with one hemoglobin molecule.
7.2 Grams (0.01 mole) of polyethylene glycol monomethyl ether of which the mean molecular weight is 750 were dissolved in 500 ml benzene, and 10 g of sodium carbonate were added to the solution. 5.5 Grams (0.03 mole) of cyanuric chloride was added to the solution while it was cooled in an ice bath and vigorously stirred. The reaction mixture was vigorously stirred overnight at room temperature. The precipitate was filtered off, and 1 l of petroleum ether (b.p. 30°-70° C.) was added to the filtrate. Precipitate of 2-O-methoxypolyethylene glycol-4,6-dichloro-S-triazine (activated polyethylene glycol) was separated, and washed sufficiently with petroleum ether. The dry amount of the activated polyethylene glycol was 11.5 g. 0.5 Gram (0.0077 mmol.) of hemoglobin was dissolved in 100 ml of borate buffer solution of pH 9.2, and 1.7 grams (1.8 mmol.) of the dry activated polyethylene glycol were added to the solution while it was cooled in an ice bath. The mixture was stirred for one hour in an ice bath, and ultrafiltration using PM-30 membrane (made by Amicon Co.) was repeated twice, and thereby the remaining hemoglobin and activated polyethylene glycol were removed. The residue contained 2.1 g of the modified hemoglobin as a dried matter. About 50 molecules of polyethylene glycol monomethyl ether were combined with one hemoglobin molecule.
19 Grams (0.01 mole) of polyethylene glycol monomethyl ether of which the mean molecular weight is 1,900 were activated using 400 ml of benzene, 10 g of sodium carbonate and 5.5 g (0.03 mole) of cyanuric chloride in the same manner as employed in Example 2, and accordingly, 24 g of the activated polyethylene glycol were obtained. 6.4 Grams (3.1 mmol.) of the activated polyethylene glycol so produced were treated with 2 g (0.031 mmol.) of hemoglobin and 200 ml of borate buffer solution of pH 9.2 in the same manner as Example 2, and 5.6 g of the modified hemoglobin were obtained. About 57 molecules of polyethylene glycol monomethyl ether were combined with one hemoglobin molecule.
50 Grams (0.01 mole) of polyethylene glycol monomethyl ether of which the mean molecular weight is 5,000 were activated using 500 ml of benzene, 10 g of sodium carbonate and 5.5 g (0.03 mole) of cyanuric chloride in the same manner as Example 2, and accordingly, 53 g of the activated polyethylene glycol were obtained. 40 Grams of the activated polyethylene glycol so produced were treated with 20 ml of 10% hemoglobin solution and 450 ml of borate buffer solution of pH 9.2 in the same manner as Example 2, and 14 g of the modified hemoglobin were obtained. About 75 molecules of polyethylene glycol monomethyl ether were combined with one hemoglobin molecule.
40 Grams (0.002 mole) of polyethylene glycol of which the mean molecular weight is 20,000 were mixed with 1 l of benzene, 10 g of sodium carbonate and 1.1 g (0.006 mole) of cyanuric chloride, and the mixture was stirred overnight at room temperature. 1 Liter of petroleum ether was added to the mixture, and precipitate formed was treated according to the same manner as employed in Example 2 to obtain 39 g of activated polyethylene glycol. 10 Grams (0.0005 mole) of the above activated polyethylene glycol were added to the mixture of 20 ml (0.00003 mole) of 10% hemoglobin and 400 ml of borate buffer solution of pH 9.2 which was previously cooled in an ice bath, and then stirred for one hour. The reaction mixture was concentrated by ultrafiltration using XM-100 membrane (made by Amicon Co.) and the modified hemoglobin in the reaction mixture was adsorbed on a column of CM-Sephadex gel which was pre-equilibrated with 0.05 M phosphate buffer solution of pH 6.0. The first fraction of elution using pH 6.3 phosphate buffer solution discarded, and the next fraction using pH 6.8 phosphate buffer solution was collected. The fraction was concentrated by using the XM-100 membrane, and 3 g of the modified hemoglobin were obtained as a dried matter. About 4 molecules of polyethylene glycol were combined with one hemoglobin molecule.
Using 12.5 g (0.005 mole) of polyethylene glycol monostearyl ester of which the mean molecular weight is 2,500, 400 ml of benzene, 5 g of sodium carbonate and 2.75 g (0.015 mole) of cyanuric chloride, the same treatment as Example 2 was carried out, and accordingly 13.5 g of activated polyethylene glycol were obtained. 10.5 Grams (0.004 mole) of the above activated polyethylene glycol were treated with 25 ml (0.04 mmol.) of 10% hemoglobin solution and 900 ml of borate buffer solution of pH 9.2 in the same manner as Example 2, and 8 g of the modified hemoglobin were obtained. About 52 molecules of polyethylene glycol monostearyl ester were combined with one hemoglobin molecule.
Using 5 g (0.005 mole) of polyethylene glycol monooleyl ether of which the mean molecular weight is 1,000, 400 ml of benzene, 5 g of sodium carbonate and 2.75 g (0.015 mole) of cyanuric chloride, the same treatment as Example 2 was carried out, and accordingly 6 g of activated polyethylene glycol were obtained. 5.3 Grams (0.002 mole) of the above activated polyethylene glycol were treated with 1.3 g (0.02 mmol.) of bovine hemoglobin (made by Sigma Co.) and 450 ml borate buffer solution of pH 9.2 in the same manner as Example 2, and 4.2 g of the modified hemoglobin were obtained. About 85 molecules of polyethylene glycol monooleyl ether were combined with one hemoglobin molecule.
12 Grams (0.003 mole) of polypropylene glycol of which the mean molecular weight is 4,000 were dissolved in 120 ml water. Using 0.0095 mole of cyanogen bromide, the solution was treated in the same manner as Example 1, and accordingly a concentrate of ultrafiltration was obtained. Using 2 g of porcine hemoglobin (made by Sigma Co.), the concentrate was treated in the same manner as Example 1, and accordingly 7 g of the modified hemoglobin were obtained. About 15 molecules of polypropylene glycol were combined with one hemoglobin molecule.
The residence time in a blood vessel and oxygem affinity of the modified hemoglobins were measured.
Two rats having an average weight of 350 g were employed as a sample. The rats were injected with 5 ml of 4-6% modified hemoglobin per kg of body weight of rat through a femoral vein, and each 0.5 ml of blood was withdrawn at 5, 10, 15, 30, 60, 90 and 120 minutes after the injection. Each blood sample was centrifuged, and the concentration of the modified hemoglobin in the plasma was determined by the cyanomethemoglobin spectral method. The data were plotted on a graph, and the half-life residence time of the injected modified hemoglobin in the plasma was determined from the graph.
TABLE 1 ______________________________________ Half-life Hemoglobin residence time ______________________________________ The material The modified hemoglobin 150 minutes of the invention of Example 1 The modifiedhemoglobin 120 minutes of Example 2 The modified hemoglobin 110 minutes of Example 3 The modified hemoglobin 210 minutes of Example 4 Control Natural hemoglobin 50 minutes Polyhemoglobin of 100 minutes Japanese Patent Publication No. 76-63920 ______________________________________
As to the modified hemoglobin solution (0.1 M NaCl solution, pH 7.40), the oxygen partial pressure at which the hemoglobin is half saturated with oxygen (P50 -value) was determined by oxygen dissociation curve which was measured by using the apparatus reported by Imai et al (K. Imai, H. Morimoto, M. Kotani, H. Watari, H. Waka and M. Kuroda, Biochem. Biophys. Acta.,Volume 200, 189-196 (1970)). The date are shown in Table 2.
TABLE 2 ______________________________________ Hemoglobin P.sub.50 ______________________________________ The material The modified hemoglobin 13.5 mmHg of the invention of Example 2 The modified hemoglobin 15.0 of Example 3 The modified hemoglobin 19.5 of Example 5 Control Natural hemoglobin 15.0 Polyhemoglobin of 9.0 Japanese Patent Publication No. 76-63920 Dextran-Hemoglobin 10.0 of Japanese Patent Publication No. 77-51016 ______________________________________
Claims (7)
1. An oxygen carrying material which comprises hemoglobin attached by a chemical reaction to a polymer selected from the group consisting of polyethylene glycol, polypropylene glycol, a copolymer of ethylene glycol with propylene glycol, an ether of one of the above polyethylene glycols with an alcohol having a carbon number of 1 to 16, an ester of one of the above polyalkylene glycols with a carboxylic acid having a carbon number of 2 to 18, and a dehydrated product of one of the above polyalkylene glycols with an amine having a carbon number of 1 to 18.
2. The material of claim 1 wherein said polymer has a molecular weight of 300-20,000.
3. The material of claim 2 wherein said molecular weight is 750-5,000.
4. The material of claim 1 wherein said hemoglobin and said polymer are attached to each other directly.
5. The material of claim 1 wherein said hemoglobin and said polymer are attached to each other by means of a cross-linking agent.
6. In a method of carrying oxygen to an animal tissue by means of an oxygen carrier, the improvement which comprises using as an oxygen carrier the attached hemoglobin polymer material of claim 1.
7. The material of claim 1 wherein said attachment of said hemoglobin to said polymer occurs by reacting said hemoglobin with said polymer which has been pretreated with cyanogen bromide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54-87910 | 1979-07-11 | ||
| JP54087910AJPS6023084B2 (en) | 1979-07-11 | 1979-07-11 | blood substitute |
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| Publication Number | Publication Date |
|---|---|
| US4301144Atrue US4301144A (en) | 1981-11-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/167,360Expired - LifetimeUS4301144A (en) | 1979-07-11 | 1980-07-10 | Blood substitute containing modified hemoglobin |
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| Country | Link |
|---|---|
| US (1) | US4301144A (en) |
| JP (1) | JPS6023084B2 (en) |
| CA (1) | CA1146858A (en) |
| DE (1) | DE3026398A1 (en) |
| FR (1) | FR2460674A1 (en) |
| GB (1) | GB2055868B (en) |
Cited By (892)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4412989A (en)* | 1981-06-10 | 1983-11-01 | Ajinomoto Company Incorporated | Oxygen carrier |
| US4598064A (en)* | 1984-06-27 | 1986-07-01 | University Of Iowa Research Foundation | Alpha-alpha cross-linked hemoglobins |
| US4600531A (en)* | 1984-06-27 | 1986-07-15 | University Of Iowa Research Foundation | Production of alpha-alpha cross-linked hemoglobins in high yield |
| US4670417A (en)* | 1985-06-19 | 1987-06-02 | Ajinomoto Co., Inc. | Hemoglobin combined with a poly(alkylene oxide) |
| US4698387A (en)* | 1983-11-10 | 1987-10-06 | Intermedicat Gmbh | Allosteric conjugates of hemoglobin and use as blood substitutes |
| US4766106A (en)* | 1985-06-26 | 1988-08-23 | Cetus Corporation | Solubilization of proteins for pharmaceutical compositions using polymer conjugation |
| US4791192A (en)* | 1986-06-26 | 1988-12-13 | Takeda Chemical Industries, Ltd. | Chemically modified protein with polyethyleneglycol |
| US4847325A (en)* | 1988-01-20 | 1989-07-11 | Cetus Corporation | Conjugation of polymer to colony stimulating factor-1 |
| US4917888A (en)* | 1985-06-26 | 1990-04-17 | Cetus Corporation | Solubilization of immunotoxins for pharmaceutical compositions using polymer conjugation |
| WO1991019505A1 (en)* | 1990-06-20 | 1991-12-26 | Research Corporation Technologies, Inc. | Modified human hemoglobin, blood substitutes containing the same, and vectors for expressing the modified hemoglobin |
| EP0512844A1 (en) | 1991-05-10 | 1992-11-11 | Celtrix Pharmaceuticals, Inc. | Targeted delivery of bone growth factors |
| US5166322A (en)* | 1989-04-21 | 1992-11-24 | Genetics Institute | Cysteine added variants of interleukin-3 and chemical modifications thereof |
| US5206344A (en)* | 1985-06-26 | 1993-04-27 | Cetus Oncology Corporation | Interleukin-2 muteins and polymer conjugation thereof |
| USRE34271E (en)* | 1984-06-27 | 1993-06-01 | University Of Iowa Research Foundation | Production of alpha-alpha cross-linked hemoglobins in high yield |
| US5234903A (en)* | 1989-11-22 | 1993-08-10 | Enzon, Inc. | Chemically modified hemoglobin as an effective, stable non-immunogenic red blood cell substitute |
| US5248766A (en)* | 1990-08-17 | 1993-09-28 | Baxter International Inc. | Oxirane-modified hemoglobin based composition |
| US5292802A (en)* | 1988-11-21 | 1994-03-08 | Collagen Corporation | Collagen-polymer tubes for use in vascular surgery |
| US5306500A (en)* | 1988-11-21 | 1994-04-26 | Collagen Corporation | Method of augmenting tissue with collagen-polymer conjugates |
| US5312808A (en)* | 1989-11-22 | 1994-05-17 | Enzon, Inc. | Fractionation of polyalkylene oxide-conjugated hemoglobin solutions |
| US5334705A (en)* | 1991-08-15 | 1994-08-02 | Duke University | Benzenetricarboxylate derivative-crosslinked low oxygen affinity hemoglobin |
| US5336603A (en)* | 1987-10-02 | 1994-08-09 | Genentech, Inc. | CD4 adheson variants |
| US5344393A (en)* | 1992-02-28 | 1994-09-06 | Alliance Pharmaceutical Corp. | Use of synthetic oxygen carriers to facilitate oxygen delivery |
| US5382657A (en)* | 1992-08-26 | 1995-01-17 | Hoffmann-La Roche Inc. | Peg-interferon conjugates |
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Also Published As
| Publication number | Publication date |
|---|---|
| DE3026398C2 (en) | 1990-09-13 |
| CA1146858A (en) | 1983-05-24 |
| GB2055868A (en) | 1981-03-11 |
| FR2460674A1 (en) | 1981-01-30 |
| JPS6023084B2 (en) | 1985-06-05 |
| FR2460674B1 (en) | 1983-06-24 |
| GB2055868B (en) | 1983-04-07 |
| JPS5612308A (en) | 1981-02-06 |
| DE3026398A1 (en) | 1981-03-26 |
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